EP1799750B1 - Polyether-functional siloxanes, polyether siloxane-containing compositions, methods for the production thereof and use thereof - Google Patents

Polyether-functional siloxanes, polyether siloxane-containing compositions, methods for the production thereof and use thereof Download PDF

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Publication number
EP1799750B1
EP1799750B1 EP04798171.7A EP04798171A EP1799750B1 EP 1799750 B1 EP1799750 B1 EP 1799750B1 EP 04798171 A EP04798171 A EP 04798171A EP 1799750 B1 EP1799750 B1 EP 1799750B1
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Prior art keywords
carbon atoms
group
polyether
branched
composition
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EP04798171.7A
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German (de)
English (en)
French (fr)
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EP1799750A1 (en
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Ekkehard MÜH
Peter Jenkner
Max Preisenberger
Burkhard Standke
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Evonik Operations GmbH
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Evonik Degussa GmbH
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon

Definitions

  • the present invention relates to novel polyether-functional siloxanes, to corresponding compositions, to the production thereof and to the use thereof.
  • Organosilanes and organofunctional siloxanes are nowadays important compounds for being able to change the properties of substrate surfaces.
  • aminosilanes such as DYNASYLAN ® AMEO, or dilute solutions thereof in water are used for coating glass fibers in order to make them compatible and reactive toward organic resins.
  • US 6 716 771 discloses the hydrophilization of the surfaces of hydrophobic dielectrics by the CMP process using special aminofunctional silane systems.
  • aminofunctional silanes and siloxanes can advantageously change the surface properties of substrates.
  • the aminofunctionality can, on the other hand, due to its nucleophility and the reactivity associated therewith, also bring about undesired effects, e.g. bring about undesired resin curing.
  • layers which contain compounds with aminogroups have a tendency to swell in a damp atmosphere.
  • Monomeric polyethersilanes are known per se ( DE 26 32 719 , EP 0 387 689 ). A distinction is made in principle between polyethersilanes with terminal hydroxy group and polyether silanes which are capped by an alkyl, aryl, alkenyl or alkynyl group. Polyether silanes with terminal hydroxy group or aqueous solutions thereof, as are described, for example, in US 5 629 437 , lead, due to strong polarity, in particular due to terminal hydroxy groups, to application problems which are comparable with those of aminosilanes.
  • the object of the invention was to provide a further way of enabling surface properties to be adjusted in a targeted manner.
  • the aim was to improve the wettability of substrate surfaces.
  • novel polyether-functional organosiloxanes according to formula I below and/or corresponding organosiloxane mixtures have been found which can be used advantageously as such, dissolved in water and/or alcohol, in a mixture with at least one monomeric organoalkoxysilane or corresponding preparation based thereon or the targeted treatment of substrate surfaces.
  • the hydrolysis alcohol can be removed from the system of aqueous solutions of present polyether siloxanes according to formula I, for example by distillation, advantageously giving a homogeneous, essentially solvent-free, i.e. low-VOC and environmentally friendly and user-friendly agent based on water for the targeted modification of substrate surfaces.
  • the present novel polyether siloxanes and compositions which comprise such polyether-functional siloxanes moreover, bring about particularly good wettability of treated substrate surfaces.
  • the present invention thus provides a linear, cyclic or branched polyether-functional siloxane or a mixture of polyether-functional siloxanes of the general formula I R[-O( 3-h)/2 Si(R 1 )(OR) h ] x [-O (3-i-j)/2 Si(R 2 )(R 3 ) i (OR) j ] y (I), in which groups R are identical or different and R is essentially H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, 2-methoxyethyl or 2-hydroxyethyl or, in the case of cyclic siloxanes, may be a silyl radical of the silyl units of the formula I, groups R 1 are identical or different and R 1 is a terminally blocked polyether group of the formula II, R 4 -O[-R 5 -O] n [(-R 6 ) m
  • Polyether siloxanes and polyether siloxane mixtures according to the invention are generally clear to opaque, slightly to moderately viscous liquids.
  • polyethersiloxanes and polyethersiloxane mixtures according to the invention can advantageously be diluted, in particular - but not exclusively - with water and/or an alcohol. Further components can also be added to compositions obtained in this way. In addition, polyethersiloxanes according to the invention or their aqueous or alcohol-containing compositions can also be added to other surface-treatment compositions as further component.
  • the present invention therefore also provides a composition which comprises at least one alcohol, preferably methanol, ethanol and/or isopropanol, and a mixture of siloxanes according to the invention of the general formula I R[-O (3-h)/2 Si(R 1 )(OR) h ] x [-O (3-i-j)/2 Si(R 2 )(R 3 ) i (OR) j ] y (I), as already explained above in more detail.
  • alcoholic compositions which have an active ingredient content of siloxanes according to formula I of from 0.5 to 99.95% by weight, preferably 1 to 99.9% by weight, particularly preferably 5 to 99.5% by weight, in particular 10 to 98% by weight, based on the composition.
  • the present invention likewise provides a composition which comprises water and a mixture of siloxanes according to the invention of the general formula I R[-O (3-h)/2 Si(R 1 )(OR) h ] x [-O (3-i-j)/2 Si(R 2 )(R 3 ) i (OR) j ] y (I), as has already been explained above in more detail.
  • an aqueous composition according to the invention has an active ingredient content of siloxanes according to formula I of from 1 to 80% by weight, particularly preferably 5 to 70% by weight, in particular 20 to 60% by weight, based on the composition.
  • Such aqueous compositions can suitably be obtained as generally clear to opaque, readily mobile to moderately viscous liquids by mixing polyethersiloxanes of the invention according to formula I with water.
  • hydrolysis alcohol produced during dilution can suitably be at least partly removed by distillation, where appropriate with fractionation and under reduced pressure.
  • Such compositions according to the invention which are otherwise essentially free from organic solvents generally have an alcohol content of less than 5% by weight, preferably ⁇ 2% by weight, particularly preferably ⁇ 0.5% by weight, in particular ⁇ 0.1% by weight, based on the composition.
  • the constituents of a composition in each case total 100% by weight.
  • the present invention further provides a composition which comprises a mixture of siloxanes according to the invention of the general formula I R[-O (3-h)/2 Si(R 1 )(OR) h ] x [-O (3-i-j)/2 Si(R 2 )(R 3 ) i (OR) j ] y (I), and at least one organoalkoxysilane from the series of alkylalkoxysilanes, preferably methyltrimethoxysilane, methyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, isobutyltrimethoxysilane and isobutyltriethoxysilane, arylalkoxysilanes, preferably phenyltrimethoxysilane and phenyltriethoxysilane, silicic esters, preferably tetramethoxysilane, tetraethoxysi
  • compositions according to the invention can advantageously comprise at least one organoalkoxysilane or corresponding hydrolysates in an amount of from 0.1 to 99.9% by weight, preferably 99.8 to 90% by weight and 10 to 0.5% by weight, particularly preferably 99.5 to 95% by weight and 5 to 1% by weight, in particular 99.2 to 98% by weight and 4 to 2% by weight, based on the composition.
  • compositions according to the invention which contain monomeric organosilane also suitably have a mixture of siloxanes according to formula I in an amount of from 0.1 to 99.9% by weight, based on the composition.
  • contents of polyether siloxanes according to the invention of from 0.2 to 10% by weight and 90 to 99.5% by weight, particularly preferably 0.5 to 5% by weight and 95 to 99% by weight, in particular 0.8 to 2% by weight and 96 to 98% by weight, based on the composition.
  • the present invention further provides a method of producing polyether siloxanes according to the invention or a polyether siloxane-containing composition according to the invention by targeted hydrolysis, condensation or cocondensation of at least one monomeric hydrolyzable silane, where
  • the reaction according to the invention is carried out by adding from 0.5 to 100 mol, particularly preferably from 1 to 80 mol, very particularly preferably from 5 to 60 mol, in particular from 10 to 50 mol, of water.
  • This method generally gives a clear to opaque, slightly to moderately viscous liquid.
  • the reaction according to the invention can be carried out in the presence of a hydrolysis and/or condensation catalyst, for example in the presence of an organic or inorganic acid or a base.
  • a hydrolysis and/or condensation catalyst for example in the presence of an organic or inorganic acid or a base.
  • a hydrolysis and/or condensation catalyst for example in the presence of an organic or inorganic acid or a base.
  • a hydrolysis and/or condensation catalyst for example in the presence of an organic or inorganic acid or a base.
  • an organic or inorganic acid or a base Preferably - but not exclusively - it is possible to use formic acid, acetic acid, hydrochloric acid, nitric acid, phosphoric acid or ammonia, alkali metal hydroxides, such as NaOH, KOH, LiOH, alkaline earth metal hydroxides, such as Ca(OH) 2 , amines, such as triethylamine, alkoxides, such as NaOCH 3 , NaOC 2
  • an inert solvent for example a corresponding alcohol with regard to the feed substances, preferably methanol, ethanol, n-propanol, isopropanol, 2-methylethanol or a mixture thereof, can be added to the reaction mixture of the reaction according to the invention.
  • the reaction is carried out at a temperature in the range from 10 to 100°C, preferably at 30 to 90°C, in particular at 50 to 80°C.
  • the reaction according to the invention is suitably carried out at a pH in the range from 1 to 12, preferably at 2 to 6 and 8 to 11, in particular at 3 to 5 and 9 to 10.5.
  • the methods known per se for determining the pH for example pH paper, chemical methods with indicators or potentiometric methods, such as pH electrodes (cf. also R. Degner, S. Leibl, "pH messen. Socate's slaughter!, VCH, Weinheim, 1995).
  • the silane of the general formula IV used is preferably at least one monomeric polyether silane from the series 3-[poly(ethylene glycol) monomethyl ether]propyltrialkoxysilane, 3-[poly(propylene glycol) mono-methylether]propyltrialkoxysilane, 3-[poly(ethylene glycol-co-propylene glycol) monomethyl ether]propyltrialkoxysilane or a mixture of at least two of the polyether alkoxysilanes, preference being given here to alkoxy groups from the series methoxy, ethoxy and propoxy.
  • polyether silanes such as 3-[(polyethylene glycol) monomethyl ether]propyltriethoxysilane, 3-[(polyethylene glycol) monoethyl ether]propyltrimethoxysilane, 2-[(polyethylene glycol) monomethyl ether]ethyltrimethoxysilane, 3-[(polyethylene glycol) monobutyl ether]propyltrimethoxysilane and 5-[(polyethylene glycol) monomethyl ether]pentyltrimethoxysilane, as starting materials.
  • Such monomeric polyether silanes are generally a mixture, where the polyether groups with terminal blocking suitably have an average degree of polymerization of the repeat units of from 3 to 30, and where the bandwidth of the individual species, determined by analytically standard methods, for example by mass spectroscopy, ranges from preferably from 1 to 100, particularly preferably from 3 to 50, in particular from 4 to 40.
  • the organoalkoxysilane of the general formula V used is preferably at least one silane from the series methyltrimethoxysilane, n-propyltrimethoxysilane, isobutyltrimethoxysilane, isobutyl-triethoxysilane, octyltrimethoxysilane, hexadecyltrimethoxysilane, perfluoropropyltri-methoxysilane, tridecafluoro-1,1,2,2-tetrahydrooctyltrimethoxysilane, vinyltrimethoxy-silane, vinylmethyldimethoxysilane, vinyltris(2-methoxyethoxy)silane, phenyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, N-(n-butyl)-3-amin
  • the polyether silane according to formula IV and (b) the organoalkoxysilane according to formula V or a mixture of organoalkoxysilanes of the general formula V are advantageously used in a weight ratio (a) to (b) of from 0.5:100 to 100:0 preferably from 5:95 to 95:5, particularly preferably from 10:90 to 90:10, very particularly preferably from 25:75 to 75:25, in particular from 40:60 to 60:40, for example - but not exclusively - ratios of 98:2, 85:15, 80:20, 70:30, 50:50, but also 40:60 and 15:85, to name but a few.
  • polyether siloxanes of the formula I which have the following combinations of functionalities: 3-[poly(ethylene glycol) monomethyl ether]propyl/hydroxy or methoxy, 3-[poly(ethylene glycol) monomethyl ether)propyl/hydroxy or ethoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/hydroxy or methoxy, ethoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/methoyl/hydroxy or methoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/methyl/hydroxy or ethoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/vinyl/hydroxy or methoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/vinyl/hydroxy or methoxy, 3-[poly(ethylene glycol) monomethyl ether]propyl/vinyl/hydroxy or methoxy, 3-[poly(ethylene glycol) monomethyl ether]propy
  • the method according to the invention is generally carried out by initially introducing the starting materials, i.e. the polyether silanes according to formula IV and the organoalkoxysilanes according to formula V and, with thorough mixing, adding water or a water/catalyst mixture in a targeted manner. It is also possible to dilute the starting material mixture used, for example by also adding a largely inert solvent, for example alcohol. However, it is also possible to initially introduce water or a water/alcohol mixture in which a catalyst is optionally present, and to meter in the starting silanes. In this connection, the pH of the reaction mixture should be in the range from 1 to 12.
  • the reaction can generally be carried out at a temperature in the range from 10 to 100°C, it being possible, if necessary, to vary the pressure. In general, the reaction is carried out over a period from 5 minutes to 8 hours. The product mixture obtained in this way can then be left to after-react, if necessary at reflux with thorough mixing.
  • the alcohol added as diluent and also the alcohol produced by hydrolysis or condensation can essentially be at least partly removed from the product mixture by distillation.
  • the distillation can be carried out with fractionation or, if necessary, under reduced pressure.
  • the amount of alcohol which is removed from the system can at the same be replaced by a corresponding amount of water.
  • Polyether siloxane obtained in this way is generally a mixture of linear, cyclic and optionally branched siloxanes.
  • Polyether siloxane according to the invention or product mixture obtained according to the invention can then be diluted with water and/or alcohol in a targeted manner.
  • At least one specific organofunctional silane preferably at least one organoalkoxysilane from the series of alkylalkoxysilanes, arylalkoxysilanes, silicic esters, fluoroalkylalkoxysilanes, aminoalkylalkoxysilanes, glycidyloxyalkylalkoxysilanes, methacryloxyalkylalkoxysilanes, mercaptoalkylalkoxy-silanes or vinylalkoxysilanes with a polyether siloxane according to the invention, and to dilute this mixture as required if appropriate with water and/or alcohol.
  • the present invention thus also provides polyether siloxanes according to the invention or corresponding siloxane mixtures or aqueous and/or alcoholic compositions according to the invention and compositions according to the invention which, besides polyether siloxanes, additionally comprise monomeric organosilanes which are obtainable by the present method.
  • Suitable substrates are, for example, but not exclusively, glass, quartz or silicon dioxide, ceramics, organically modified ceramics, speciality ceramics, such as SiC, SiOC, Si 3 N 4 , SiBN, SiBNC, BN, SiAlO, SiZrO, SiTiO, but also fillers and pigments, such as calcium sulfate, calcium carbonate, iron oxides, titanium oxides, aluminum oxides, silicon oxides, magnesium oxides, zirconium oxides, tin oxides, germanium oxides, zinc oxides, talc, kaolin, corundum, barite, wollastonite, indium-tin oxide, metals, such as iron, iron alloys, in particular steel, aluminum, aluminum alloys, titanium, titanium alloys, magnesium, magnesium alloys, copper, copper alloys, silver, silver alloys, gold, gold alloys, platinum, platinum alloys, polar plastics, such as, for example, polyesters or polyimide, polycarbonate, polyacrylates and polymethacrylates
  • the preferably treated substrates also include layers produced by CVD and SPIN-on processes which, inter alia, can contain Si, O, C and N as such or in the form of corresponding compounds, in particular those layers which are used as dielectric in electronic components, i.e. on silicon surfaces, such as that of wafers.
  • the treatment can here be carried out, for example, by the chemical-mechanical polishing of wafer surfaces during the manufacture of semiconductors.
  • Polyether siloxanes according to the invention or corresponding compositions according to the invention can be applied to a substrate surface for example - but not exclusively - by dipping, flow coating, sprinkling, spraying, centrifugation, polishing, doctoring, brushing, painting or collandering. Drying can then suitably take place at a temperature between 10 and 220°C, preferably between 20 and 150°C. This generally gives layers with a thickness of from 20 to 0.01 ⁇ m. The good wettability is usually evident as early as during application of the polyether-functional siloxanes according to the invention and of the compositions, as a result of which an extremely homogeneous layering can be achieved in a particularly advantageous manner.
  • the surface of the coated object or substrate can generally be coated very readily with polar to nonpolar media depending on how the composition of the condensates and/or cocondensates, i.e. the combination of the functionalities in the siloxanes, is chosen. Moreover, such layers are advantageously characterized by excellent adhesion promoting properties.
  • the present invention further provides the use of polyether siloxanes according to the invention and said compositions according to the invention for the treatment of substrate surfaces, i.e. in particular for a targeted modification of the properties of a surface, preferably of metals, such as silicon, aluminum, iron, titanium, magnesium, zinc, tin, copper, silver, gold, platinum, nickel, chromium, vanadium, tungsten, of alloys, such as iron alloys, steel, aluminum alloys, magnesium alloys, titanium alloys, copper alloys, silver alloys, gold alloys, platinum alloys, of conventional ceramics or speciality ceramics, such as SiC, SiOC, Si 3 N 4 , SiBN, SiBNC, BN, SiAlO, SiZrO, SiTiO, of artificial stone, of glass, of glass and mineral fibers, of construction materials, of building structures, as coating composition, as additive in coating compositions, as wetting agent for surfaces, as additive in wetting agents, as lubricant, as additive in lubricants, and in hydraulic fluid
  • epoxy molding compounds in the manufacture of wafers, semiconductors and chips, for the coating of optical lenses and of contact lenses, for the coating of electrolytic copper foils for printed circuit boards, for the silanization of fillers and pigments, such as calcium sulfate, calcium carbonate, iron oxides, titanium oxides, aluminum oxides, silicon oxides, magnesium oxides, zirconium oxides, tin oxides, germanium oxides, zinc oxides, talc, kaolin, corundum, barite, wollastonite, indium-tin oxide, and for the improvement of the rheological properties of dispersions.
  • fillers and pigments such as calcium sulfate, calcium carbonate, iron oxides, titanium oxides, aluminum oxides, silicon oxides, magnesium oxides, zirconium oxides, tin oxides, germanium oxides, zinc oxides, talc, kaolin, corundum, barite, wollastonite, indium-tin oxide, and for the improvement of the rheological
  • the present invention thus also provides agents or articles based on the use according to the invention or use of a polyether siloxane according to the invention or a corresponding composition according to the invention.
  • DYNASYLAN ® F 8261 tridecafluoro-1,1,2,2-tetrahydrooctyltriethoxysilane
  • DYNASYLAN ® AMEO 3-aminopropyltriethoxysilane
  • DYNASYLAN ® MTES methyltriethoxysilane
  • DYNASYLAN ® TRIAMO 3-[2-(2-aminoethylamino)-ethylamino]propyltrimetoxysilane
  • DYNASYLAN ® 1151 aminofunctional siloxanes in water
  • DYNASYLAN ® HS 2775 triaminofunctional siloxanes in water
  • Example/ comp example Treatment agent Organofunctionalities of the siloxane and active ingredient Contact angle ⁇ [°] 7 (blank value) - - 33 ⁇ 2° 8 from example 1 polyether 6 ⁇ 1° 9 from example 3 polyether/aminoalkyl 20 ⁇ 1° 10 from example 6 polyether/triaminoalkyl 25 ⁇ 1° 11 (comp.

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EP04798171.7A 2004-10-08 2004-11-05 Polyether-functional siloxanes, polyether siloxane-containing compositions, methods for the production thereof and use thereof Not-in-force EP1799750B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004049427A DE102004049427A1 (de) 2004-10-08 2004-10-08 Polyetherfunktionelle Siloxane, polyethersiloxanhaltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung
PCT/EP2004/052832 WO2006037380A1 (en) 2004-10-08 2004-11-05 Polyether-functional siloxanes, polyether siloxane-containing compositions, methods for the production thereof and use thereof

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EP1799750A1 EP1799750A1 (en) 2007-06-27
EP1799750B1 true EP1799750B1 (en) 2014-09-17

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US (1) US8236918B2 (ja)
EP (1) EP1799750B1 (ja)
JP (1) JP5032325B2 (ja)
KR (1) KR100898442B1 (ja)
CN (2) CN102516776A (ja)
DE (1) DE102004049427A1 (ja)
ES (1) ES2524299T3 (ja)
HK (1) HK1110611A1 (ja)
NO (1) NO20072379L (ja)
WO (1) WO2006037380A1 (ja)

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ES2524299T3 (es) 2014-12-05
CN101048445B (zh) 2012-07-04
WO2006037380A1 (en) 2006-04-13
JP2008516019A (ja) 2008-05-15
KR100898442B1 (ko) 2009-05-21
CN102516776A (zh) 2012-06-27
EP1799750A1 (en) 2007-06-27
JP5032325B2 (ja) 2012-09-26
US8236918B2 (en) 2012-08-07
NO20072379L (no) 2007-05-08
US20090030162A1 (en) 2009-01-29
KR20070097410A (ko) 2007-10-04
DE102004049427A1 (de) 2006-04-13
HK1110611A1 (en) 2008-07-18
CN101048445A (zh) 2007-10-03

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